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Synthesis and Cholinesterase Inhibitory Activity of New 2-Benzofuran Carboxamide-Benzylpyridinum Salts Publisher Pubmed



Abedinifar F1 ; Farnia SMF1 ; Mahdavi M2 ; Nadri H3 ; Moradi A3 ; Ghasemi JB1 ; Kucukkilinc TT4 ; Firoozpour L5 ; Foroumadi A5, 6
Authors
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Authors Affiliations
  1. 1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  2. 2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
  4. 4. Department of Biochemistry, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey
  5. 5. Department of Medicinal Chemistry, Faculty of Pharmacy and The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran
  6. 6. Department of Medicinal Chemistry, Faculty of Pharmacy and Neuroscience Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, Kerman, Iran

Source: Bioorganic Chemistry Published:2018


Abstract

A series of benzofuran-2-carboxamide-N-benzyl pyridinium halide derivatives (6a-o) are synthesized as new cholinesterase inhibitors. The synthetic pathway involves the reaction of salicylaldehyde derivatives and ethyl bromoacetate, followed by hydrolysis and amidation with 3- and 4-picolyl amine. Subsequently, N-((pyridin-4-yl) methyl) benzofuran-2-carboxamide and substituted N-((pyridin-3-yl) methyl) benzofuran-2-carboxamides reacts with benzyl halides to afford target compounds (6a-o). The chemical structures of all derivatives were confirmed by spectroscopic methods. The studies reveal that some of the synthesized compounds are potent butyrylcholinesterase inhibitors with IC 50 values in the range of 0.054–2.7 µM. In addition, good inhibitory effects on Aβ self-aggregation are observed for 6h and 6k (33.1 and 46.4% at 100 µM, respectively). © 2018 Elsevier Inc.
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